1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3,3-diethyl-4β-(α-methylstyryl)-2-azetidinone | 241156-29-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3,3-diethyl-4β-(α-methylstyryl)-2-azetidinone
• 英文别名: (4R)-1-[(R)-[(4R,5S)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]-(1,3-dithian-2-yl)methyl]-3,3-diethyl-4-[(E)-1-phenylprop-1-en-2-yl]azetidin-2-one
• CAS: 241156-29-6
• 化学式: C₃₁H₄₅NO₅S₂
• 分子量: 575.834
• InChiKey: UVTJCKIKCRKKGJ-PJXYUJMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.34
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  57.23
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3,3-diethyl-4β-(α-methylstyryl)-2-azetidinone 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 以85%的产率得到3,3-diethyl-4β-(trans-α-methylstyryl)-2-azetidinone
  参考文献：
  名称：

  d-Glucosamine propanedithioacetal, an efficient chiral auxiliary in β-Lactam chemistry1Dedicated to Professor Sir Derek H. R. Barton.1

  摘要：

  The synthesis of some monocyclic beta-lactams (monobactams) by the Staudinger reaction using D-glucosamine propanedithioacetal as chiral auxiliary is reported. The influence of several radicals at C-3, C-4, and C-1' (sugar moiety) as well as other structural aspects are considered in relation to the antielastase activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00264-8
• 作为产物：
  描述：

  D-glucoasamine hydrochloride 在 TEA 、 对甲苯磺酸 作用下， 以 甲苯 为溶剂， 反应 18.0h， 生成 1<(1',2'-dideoxy-3',4';5',6'-di-O-isopropylidene-1'(1,3-propanedithio))-D-2'-glucosyl>-3,3-diethyl-4β-(α-methylstyryl)-2-azetidinone
  参考文献：
  名称：

  d-Glucosamine propanedithioacetal, an efficient chiral auxiliary in β-Lactam chemistry1Dedicated to Professor Sir Derek H. R. Barton.1

  摘要：

  The synthesis of some monocyclic beta-lactams (monobactams) by the Staudinger reaction using D-glucosamine propanedithioacetal as chiral auxiliary is reported. The influence of several radicals at C-3, C-4, and C-1' (sugar moiety) as well as other structural aspects are considered in relation to the antielastase activity. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(98)00264-8